carbalexin C

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: carbalexin C
• 英文别名: carbalexine C；2-hydroxy-6-methoxy-3-methylcarbazole；6-methoxy-3-methyl-9H-carbazol-2-ol
• 化学式: C₁₄H₁₃NO₂
• 分子量: 227.263
• InChiKey: AIVUYXSNEZKNBV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  45.2
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  carbalexin C 在 titanium(IV) isopropylate 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 四氢呋喃 、 甲醇 、 水 、 甲苯 为溶剂， 反应 46.0h， 生成 claulansine F
  参考文献：
  名称：

  Pyrano[3,2-a]carbazole alkaloids as effective agents against ischemic stroke in vitro and in vivo

  摘要：

  A series of pyrano[3,2-a]carbazole alkaloids were designed and synthesized as analogues of Claulansine F (Clau F, 10a) isolated from Clausena lansium. Some of compounds showed strong neuroprotective effects and were promising agents against ischemic stroke. Among these compounds, 7c was the most active in inhibiting the programmed death of PC12 cells and primary cortical neurons. This compound induced neuroprotection following ischemic reperfusion and decreased neurological deficit scores in treated animals. Furthermore, 7c could penetrate the blood-brain barrier (BBB) in rats, and its exposure in the brain was 4.3-fold higher than that in plasma. More importantly, compared to edaravone, 7c exhibited stronger free radical scavenging activity. Our findings suggest that 7c may be promising for further evaluation as an intervention for ischemic stroke. (C) 2017 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2017.11.084
• 作为产物：
  描述：

  4-氨基-5-氯-2-甲氧基苯甲酸 在 palladium diacetate 、 三溴化硼 、 potassium carbonate 、 sodium t-butanolate 、 tri tert-butylphosphoniumtetrafluoroborate 作用下， 以 二氯甲烷 、 N,N-二甲基乙酰胺 、 氯苯 、 甲苯 为溶剂， 反应 57.0h， 生成 carbalexin C
  参考文献：
  名称：

  对映选择性钒催化的氧化偶联：发展和机制的见解。

  摘要：

  据报道，用于苯酚的对映选择性氧化偶合反应的反应性更强的手性钒催化剂的发展，最终导致与布朗斯台德或路易斯酸添加剂结合的简单单体钒物种。发现所生成的钒配合物会影响不对称氧化邻位-邻位简单的酚和2-羟基咔唑的对映选择性良好至极好。该机理的实验和量子力学研究表明，添加剂使钒单体聚集。另外，在碳-碳键形成之前，涉及单重态到三重态的交叉。导致对映体产物的两个最低能量的非对映体过渡态在涉及较小的对映体的路径上有很大不同，所述较小的对映体在两个酚部分之间具有较大的扭转应变。

  DOI：

  10.1021/acs.joc.8b02083

文献信息

• Transition Metals in Organic Synthesis, Part 91:¹ Palladium-Catalyzed Approach to 2,6-Dioxygenated Carbazole Alkaloids - First Total Synthesis of the Phytoalexin Carbalexin C
  作者：Hans-Joachim Knölker、Marika Schmidt

  DOI：10.1055/s-0029-1217810

  日期：2009.9

  The palladium(0)-catalyzed C-N bond formation and palladium(II)-catalyzed oxidative cyclization provide an efficient route to a series of 2,6-dioxygenated carbazole alkaloids including the first total synthesis of the phytoalexin carbalexin C.

  钯 (0) 催化的 CN 键形成和钯 (II) 催化的氧化环化为一系列 2,6-二氧化咔唑生物碱提供了有效途径，包括植物抗毒素卡巴莱辛 C 的首次全合成。
• Synthesis of 1,1′- and 2,2′-Bicarbazole Alkaloids by Iron(III)-Catalyzed Oxidative Coupling of 2- and 1-Hydroxycarbazoles
  作者：Christian Brütting、Raphael F. Fritsche、Sebastian K. Kutz、Carsten Börger、Arndt W. Schmidt、Olga Kataeva、Hans-Joachim Knölker

  DOI：10.1002/chem.201704554

  日期：2018.1.9

  We describe the synthesis of 1,1′‐ and 2,2′‐bicarbazoles by oxidative homocoupling of 2‐ and 1‐hydroxycarbazoles. The oxidative coupling using catalytic amounts of F16PcFe can be applied to both groups of substrates. Although F16PcFe generally provides the best yields for the synthesis of 1,1′‐bicarbazoles, di‐tert‐butyl peroxide affords better results for the 2,2′‐bicarbazoles. In our study, we have

  我们描述了通过2-羟基和1-羟基咔唑的氧化均偶联来合成1,1'-和2,2'-联咔唑。使用催化量的F 16 PcFe的氧化偶合可应用于两组基材。F尽管也16 PCFE通常提供的1,1'- bicarbazoles合成最好的产率，二-叔过氧化丁酯为2,2'-联咔唑提供了更好的结果。在我们的研究中，我们已经完成了双卡巴菌毒素A-C，双糖胺B，2,2'-二羟基-7,7'-二甲氧基-3,3'-二甲基-1,1'-联咔唑，双吡a啉C的首次合成，和双西马嘌呤。铁链烯酮的催化偶合提高了8,8'-二甲烯胺的合成能力，并提供了前所未有的癸酰基产物。1-羟基咔唑的氧化偶合生成了比屈烯醇和第一个总合成的比莫拉佛林B和D.
• Synthesis of the Pyrano[3,2-a]carbazole Alkaloids Koenine, Koenimbine, Koenigine, Koenigicine, and Structural Reassignment of Mukonicine
  作者：Hans-Joachim Knölker、Christian Schuster、Marika Rönnefahrt、Konstanze Julich-Gruner、Anne Jäger、Arndt Schmidt

  DOI：10.1055/s-0035-1560359

  日期：——

  Using the palladium(II)-catalyzed oxidative cyclization of a diarylamine and the annulation of a dimethylpyran ring by Lewis acid promoted reaction with prenal as key steps, the total syntheses of the 6-oxygenated pyrano[3,2-a]carbazole alkaloids koenine and koenimbine, and of the 6,7-dioxygenated pyrano[3,2-a]carbazole alkaloids koenigine and koenigicine (koenimbidine, koenidine) were achieved. Moreover, these studies led to an improved synthetic route to the 2,6-dioxygenated carbazole alkaloid glycozolidol. Mukonicine, originally published as 6,8-dimethoxypyrano[3,2-a]carbazole, was found to be identical with koenigicine.
• Enantioselective Vanadium-Catalyzed Oxidative Coupling: Development and Mechanistic Insights
  作者：Houng Kang、Madison R. Herling、Kyle A. Niederer、Young Eun Lee、Peddiahgari Vasu Govardhana Reddy、Sangeeta Dey、Scott E. Allen、Paul Sung、Kirsten Hewitt、Carilyn Torruellas、Gina J. Kim、Marisa C. Kozlowski

  DOI：10.1021/acs.joc.8b02083

  日期：2018.12.7

  vanadium catalyst for enantioselective oxidative coupling of phenols is reported, ultimately resulting in a simple monomeric vanadium species combined with a Brønsted or Lewis acid additive. The resultant vanadium complex is found to effect the asymmetric oxidative ortho–ortho coupling of simple phenols and 2-hydroxycarbazoles with good to excellent levels of enantioselectivity. Experimental and quantum

  据报道，用于苯酚的对映选择性氧化偶合反应的反应性更强的手性钒催化剂的发展，最终导致与布朗斯台德或路易斯酸添加剂结合的简单单体钒物种。发现所生成的钒配合物会影响不对称氧化邻位-邻位简单的酚和2-羟基咔唑的对映选择性良好至极好。该机理的实验和量子力学研究表明，添加剂使钒单体聚集。另外，在碳-碳键形成之前，涉及单重态到三重态的交叉。导致对映体产物的两个最低能量的非对映体过渡态在涉及较小的对映体的路径上有很大不同，所述较小的对映体在两个酚部分之间具有较大的扭转应变。
• Pyrano[3,2-a]carbazole alkaloids as effective agents against ischemic stroke in vitro and in vivo
  作者：Yingda Zang、Xiuyun Song、Chuangjun Li、Jie Ma、Shifeng Chu、Dandan Liu、Qian Ren、Yan Li、Naihong Chen、Dongming Zhang

  DOI：10.1016/j.ejmech.2017.11.084

  日期：2018.1

  A series of pyrano[3,2-a]carbazole alkaloids were designed and synthesized as analogues of Claulansine F (Clau F, 10a) isolated from Clausena lansium. Some of compounds showed strong neuroprotective effects and were promising agents against ischemic stroke. Among these compounds, 7c was the most active in inhibiting the programmed death of PC12 cells and primary cortical neurons. This compound induced neuroprotection following ischemic reperfusion and decreased neurological deficit scores in treated animals. Furthermore, 7c could penetrate the blood-brain barrier (BBB) in rats, and its exposure in the brain was 4.3-fold higher than that in plasma. More importantly, compared to edaravone, 7c exhibited stronger free radical scavenging activity. Our findings suggest that 7c may be promising for further evaluation as an intervention for ischemic stroke. (C) 2017 Elsevier Masson SAS. All rights reserved.